Mercury compound of nitro-orthocresols



Fatented Apr. 3, I934 MERCURY COMPOUND OF NITRO-ORTHO CRESOLS George W. Raiziss, Philadelphia, Pa., assignor to Abbott Laboratories, North Chicago, 111., a corporation of Illinois No Drawing. Application June 21, 193,2, Serial No. 618,565

3 Claims. (Cl. 260 13) My invention relates to certain new comtreating either the acetoxy or anhydro-hydroxy' pounds which have been found to be especially derivatives with a halide acid, thus: effective as bactericidal and bacteriostatic agents, CflH2 0H3 NO2 O Na HgOH +2101 particularly in combating infectious diseases, and CuHz-CHaNO2OHHgC1+NaO1+H*O. relates more particularly to mercury compounds The following examples illustrate my invem of nitro-cresols. tion;

In my Patent No. 1,554,293, granted September Example 22, 1925, there is described diacetoxy-mercurid-nitro-ortho-cresol. Upon discovery that the Using S-nitro-ortho-cresol prepared by nitra- 10 compound produced as described in said patent tion of ortho cresol in benzene using dilute nitric did not in fact conform to said formula, this acid (Berichte-40,43l9), I prepared by the above patent was reissued as No. 17,563, dated January described method acetoxy-mercuri-5-nitro- 14, 1930. In my Patent No. 1,630,072, granted ortho-cresol: May 2-1, 1927, there are described certain mer- OH 15 cury derivatives of S-nitro-ortho-cresol. All of 3 these derivatives were found to have excellent OH properties as bactericides. However, my continued research has developed the fact that other OO CH3 isomeric mercury derivatives of nitro-orthocresols may likewise prepared a that such consisting of white silky needles, decomposing substances also are highly eiiective as bacteat C" and anhydro hydroxy mercuri 5 ricides. -i These new nitro-cresol derivatives difier from mom Ortho creso each other, sometimes to a considerable extent, CH3 25 in their physical, chemical and bacteriological 0 so properties, and may be represented by the typical 0 formula: 1

RngX g H 30 for the mono-mercury derivatives, and 5 R (HgX)2 The latter product consists of cream colored,

minute needles, insoluble in water, soluble in difor the Oily deriVatiVeS, W fi R plute alkalies, producing a bright yellow solution resents 5-nitro-ortho-cresol and X represents in 9, dilution of 13500, Van acetoxy group, CHsCQO-, a halog n, a y- The foregoing example will suggest various droxy g oup OH, 0 Wh n w e 0f Waother modifications of the same general method ter is removed from the latter, an anhydro-hyto a person skilled in the art. droxy group O. The halide-mercuri and hydroxy-mercuri com- In p p these new products, I mercurate pounds are prepared as indicated by the above re- 4Q any of the isomers of a nitro-ortho-cresol and ti produce first an acetox -m rcu i C mp The compounds described above are usually This is then converted into an anhydro-hydroxydispensed in the form of their sodium salts in mercuri derivative according to the following aqugous l ti th preparation of hich 111 reactions: be obvious to those skilled in the art. 45- Changes and variations coming within the OOC-OH o Bhg8ha 1o g H -H o h onficmc00H spirit of my invention will doubtless suggest them- O N 0H selvesto those stalled in the art. Hence, I do 3 o6E-cH3 No2-0H lhrfi-o omwnio not WlSh to be limited to the specific embodiments disclosed herein or uses mentioned except 5 The hydro f i f a ff to the extent set forth in the appended claims, as me m akame which are to be interpreted as broadly as the Solutlon, as followsstate of the art will permit.

OtH2CHaNOiOHHgCOOCHa+2NaOH-) The nomenclature used in defining the above CHQCH3 NO*ONaHgOH+OHPCooNal'mo' compounds is that employed in the inventors 55; The halogen derivatives may be formed by Reissue Patent No. 17,563, areissue of Patent No.

2;. wherein the production of 2. A substance which may be represented by nitro-ortho-cresol is disclosed, said nomenclature th t t l formula; being that used in the 3d edition of Beilstein. CH I claim as my invention: 3 1. A compound which may the formula:

be represented by wherein is the nucleus of 3. A substance which may be represented by 0H3 the structural formula:

X is acetoxy, a halogen, hydroxy or anhydrohydroxy, and n represents a whole number not greater than 2. GEORGE W. RAIZISS.

CERTIFICATE OF CORRECTION.

Patent No. 1,953,263. April 3, 1934.

GEORGE W. RAIZISS.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, line 56, after "acetoxy" insert thevword hydroxy; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 15th day of. May, A. D. 1934.

Bryan M. Battey Seal Aetin Commissioner oi Patents, 

